While other media rushed online, Condé Nast dug in its Louboutin heels. Now, with its much ballyhooed iPad play stalling out--so 2010!--the knives are out for digital wonder boy Scott Dadich.

Not long after Scott Dadich was appointed executive editor of digital magazine development for all of Condé Nast, “the tops of the mastheads,” as the senior editorial staffs are called, filed into the company’s fourth-floor lecture hall for a series of meetings. Condé’s new iPad king was holding court.

This wasn’t the first time the tastemakers of 4 Times Square had met Mr. Dadich. He’d been shopping “that Wired thing” around the company since it debuted in iTunes’ App Store in May 2010 to considerable fanfare and a flurry of downloads.

But this time, Mr. Dadich faced a few more sets of crossed arms.

Mr. Dadich’s coronation, in August 2010, had come with a big window office on the seventh floor and a mandate to lead the brands that Si Newhouse built into the brave new world of the tablet, a device so shiny and elegant it made Condé’s stable of glossies look dull by comparison. Not surprisingly, Mr. Dadich’s arrival also brought a share of resentment his way in no small part because, even in the pages of this paper, his ascent from Wired, where he had spun a lagging title into ASME gold as creative director, was presented in near-messianic terms.

In a profile of Mr. Dadich in The Observer last August, Evan Smith, his former boss at Texas Monthly, likened Mr. Dadich to a “combination of Jesus and Pelé” before deciding, a moment later, that a comparison to Miles Davis and Frank Lloyd Wright was more apt. Legendary Esquire art director George Lois was, if possible, even more effusive about Condé’s new It Boy, declaring, “With a talent like Scott, magazines will never die.”

Within 4 Times Square, such praise was met with a degree of skepticism, but the breathless optimism among the Condé kingmakers who backed Mr. Dadich was to be expected. It’s hard to find a print dinosaur that doesn’t drool a little, post-recession, over the possibility of wading into a teeming new revenue stream. But Condé Nast felt the pressure more acutely than most. Mr. Newhouse’s puritanical if lavish stewardship of his beloved titles had left the company playing a careful game of wait-and-see through roughly the first three-quarters of the Internet revolution.

Condé’s initial flirtations with the web had been coy and tentative. Rather than sully established titles like Gourmet and Vogue, the company launched new sites, including Epicurious.com and Style.com, as a way of protecting its spoiled progeny from the rough-and-tumble Internet.

While Condé Nast was far from the only media company to find its established business model upended by the web, it appeared to be more paralyzed than most by the shift, perhaps because, in some ways, the rules of online media ran counter to the entire culture of the company. Where Condé Nast had been built on the notion of exclusivity—the idea that its gatekeepers held the keys to a sort of private club, doling out access to readers one glamorous photo spread or finely-turned phrase at a time—the Internet was messy, democratic and fundamentally untamable. Marquee titles like Vanity Fair, Vogue and the New Yorker seemed obsessed with hierarchies. The web obliterated them. Mr. Newhouse’s painstakingly constructed and assiduously policed royal court had come under threat—the villagers were massing at the gates!—and the ambivalence within the company was apparent: every attempt to welcome in the hoi polloi was met with an opposing impulse to head for higher ground on the castle wall.

Former web editors are still baffled by budgets that allowed for a suite to cover the Oscar party at Morton’s but can’t seem to assign to an extra desk for an online editor. Permission was required from the tech side before any print content was posted online. Nine months could crawl by before a request for an RSS feed or comment system on a site made its way through the system. Up until a few years ago, editorial staffers were shackled to a bloated corporate content management system that “forces web editors to spend enormous amounts of time wrangling the system instead of creating content,” according to one insider.

When individual titles began make their own forays into the web, they did so gingerly, slapping up what seemed to be placeholder sites geared mostly to picking up subscriptions. Meanwhile, rivals were popping up everywhere. “The biggest shame was that Vogue wasn’t Net-a-porter,” a former Condé Nast print editor told The Observer. “That was the missed opportunity of the century.”

The iPad, then, promised more than just a do-over. It was a chance for redemption. See what we did there? We’re not extinct! And for all his technical wizardry, Steve Jobs seemed a worthy partner, with his refined aesthetic and affinity for gated communities not unlike the neighborhood Condé Nast had occupied for years. The iPad seemed to promise that, both financially and culturally, the company could resort to its comfy old habits and maybe still survive.

Condé Nast’s digital efforts have been restructured so many times, it’s hard to keep the chronology straight. But call it CondéNet or Condé Nast Digital—as the digital arm has been named at various times—in some ways, it’s the same as it ever was.